Tips For Working Full-Time While Traveling Full-Time

Danny DoverApril 19, 2012

Although I don’t remember which country I was in, I remember the conversation very well. I was staying at an Airbnb rental with an extremely friendly host. I sat in a funny colored chair in my host’s living room while I worked on the emptying my e-mail inbox. My host walked into the room and smugly ordered me to stop working.

“You are on vacation, stop working!”, said the host with a smile that showed he was not really joking.

“I have to handle this first, then I will go out and about!”, I replied with an appreciative smirk.

“This is what I don’t understand about technology people, they are always working and never having fun!”

My host then picked up his briefcase and headed out the door to work. It was a Sunday morning.

I smiled to myself with a brief sense of enlightenment. Who was the one that really was working too much?

I am currently committing an act that many people have advised me not to attempt. I am traveling full-time while working on a start-up. My co-founder, Sam is essentially doing the same thing. And you know what is weird? Despite the warnings, we are doing quite well!

Notice that our toolset is essentially the same as most tech entrepreneurs who are not traveling. This wasn’t done on purpose but it does show how the Internet makes it essentially the same experience to work 1 mile apart or 5,000 miles apart.

So What Exactly Are You Doing?

Sam is in Maui right now taking kite surfing lessons while I am in Rome checking off more bucket list items. We are still working 40ish hours a week but now when we burn out after several hours of working hard, we take more exciting breaks. Below is my schedule from today.

Today I woke up, shot off a series of e-mails to my co-founder (who as I mentioned is in Maui, Hawaii), our designer (who is in Calgary, Alberta), our videographer (Seattle, Washington), several clients (Chicago, Illinois and Los Angeles, California) had a phone call with my sister (Nashville, Tennessee) and then sent a Facebook message to a friend I will be meeting in Switzerland.

I then showered, hopped on the metro and went to see the Pope speak in Saint Peter’s Square in Vatican City. I am not sure what he said (I don’t speak Pope) but I did see a Nun do a fist pump so I am assuming his speech was good. :-p

I then did about three hours of work at a cafe before feeling restless and decided to take a jog up the Spanish Steps. I then grabbed some delicious pizza from a restaurant a stranger had recommended and walked back to my room to relax and do some additional work. All of this happened before my co-founder even woke up. He is 12 hours behind me (in timezones and in life ;-p) so without even meaning to we make progress on our company almost 24 hours a day (at least in theory).

The key here is that these are not atypical days. Last week I was in Florence and had a similar schedule. Instead of jogging the Spanish Steps, I biked with a friend around the city. The week before that, I had a similar routine in Stockholm, Sweden. Before that I was in Prague. You get the picture.

The process is I do multiple hour stints of work that require high concentration and then once I inevitably burn out, I go on a fun adventure. I then repeat the process. Work hard, play even harder.

What Are The Hard Parts?

It is not a perfect system and we occasionally run into issues but really it is not any harder than when we worked at the same desk in Seattle years ago. We have the advantage that our individual skillsets complement each other well and we are constantly making an extended effort to make sure we are communicating well.

Counterintuitively, it is not the distance or timezones that are hard, it is the subtleties of language that work against us. Was that a joke? Is he taking on more work than he should? Is that something I should have handled better? All of these questions can result from a simple miscommunication caused by a lack of a punctuation or the inability to see a facial expression.

To correct for these, we do the following.

Workflow Tips:

We host most of our meetings over video chat so that we can see body language

We make a concerted effort to over-communicate

We rely on the experiences we have had working together in person to understand what is happening when we work remotely

We talk as plainly and honestly as we can

We use a lot of bulleted lists in e-mails

We verify we have Internet connectivity 10 minutes before all important meetings

So the next time someone tells you it is impossible to start a company and travel at the same time, tell them they are wrong. It is hard, but with a few simple tweaks to routine and a lot of hard work, working successfully while traveling becomes possible.

—

P.S. That image is of me at the top of Duomo in Florence. If you look closely, you will notice the strap of my laptop bag around my shoulder. Yes, I took my computer to the top of Florence :-p I had just finished working at a cafe!

Great tips, Danny. I’m working on going remote myself, yet I wasn’t sure how I’d be able to handle traveling to new places and working at the same time. It sounds like you’re doing just fine with it!

I might be dealing with an employer and a boss, so that could be a bit more difficult if I travel outside the US.

http://www.lifelisted.com/ Danny Dover

Awesome! If your experience is anything like mine, it will be one of the best decisions you ever make. :-)

I have worked remotely while having a boss (AT&T and SEOmoz) as well as while working for myself. It is very doable, it is just not the four hour work week that others talk about.

Andrew Smirnov

Danny, ever since college you seem to always have something up your sleeve, including this blog, you work and travel. I think that’s a great list, I don’t travel the world but I do travel the US, and another tip I can add is combine your work environment with the ambiance of your surroundings. For example if you need to do reports, or write-ups that may not require internet connectivity (unless you have a data card) you can stituate yourself in an environment where people are relaxing, there is scenery around, and/or you can get yourself a refreshment. This could be a park, a cafe, a hotel lobby, museum enterance. I find when I surround myself in these social zones I can tune in on my work but feel much more relaxed and energized by the surroundings. I think we often look for things called work/life balance, or a distinction from work and play, but if you think about nothing in life really works that way, the complete separation actually makes you switch gears I think is what causes people to dread going to work. I think the key is to have a layer between the two (a mixed zone per say) where you get work done without the complete immersion of the traditional workspace.

http://www.lifelisted.com/ Danny Dover

Hey Andrew! Really good to hear from you.

“a distinction from work and play, but if you think about nothing in life really works that way, the complete separation actually makes you switch gears I think is what causes people to dread going to work. I think the key is to have a layer between the two (a mixed zone per say) where you get work done without the complete immersion of the traditional workspace.”

I think you are really on to something there. I think is the switch between black and white, work and play that makes one seem so great and one seem so awful. Instead you make a great point by recommending living in the grey.

Cheers bud!

http://www.dcdigitalconsulting.com Daniel Christopher

Great tips Danny! I’ve been traveling (part-time) and working full time. I just got back from a week in Puerto Rico where I was visiting a friend. The hardest part is maintaining the mindset that you aren’t on a real vacation; that there are obligations you need to take care of during the day. The temptation of being surround by so many new people and new things to see continues to be the hardest obstacle to overcome. It takes a strong mindset and developing strong work habits to adapt.

One tip I’d add:

Scout several internet hot-spots within the area you will be traveling. I’ve had too many instances where I saw on Yelp that a local coffee shop provided free wifi, only to be disappointed to find out it was too slow to work from. You can’t be productive when pages take seconds to load and especially if you rely on Skype or any video conferencing tool for work. So always have plan A, B and even C.

http://mslistologist.com Annette | Bucket List Journey

Great post, but I mostly love that you made it to the top of the Duomo ;)

Good tips. I assume you spend lot of time in travelling via plane, trains and buses. How do you make the best use of this time? Like do you work on plane and other public transport or use that time for relaxing and planning out the rest of the day or the next day. Are you a very organized person, everything planned out in advance or you use just go with the flow. How do you avoid getting distracted by new places, things and people around you? Whenever i have tried working during holiday or while travelling, it never really worked.

http://www.lifelisted.com/ Danny Dover

Hey Himanshu :-)

I get a lot of work done during my transit days. This mostly takes place at stations (bus/train or airports) and then on the ride itself.

> Are you a very organized person, everything planned out in advance or you use just go with the flow.

I have everything organized into projects but the tasks are go with the flow.

> How do you avoid getting distracted by new places, things and people around you?

I don’t have this mastered but typically am good about avoiding distractions in transport or at cafes. Headphones and lyric-less music do the trick for me.

> Whenever i have tried working during holiday or while travelling, it never really worked.

Just like anything, it takes practice.

Hope that helps!

http://www.joytia1999.com Joy Elly – Tia 1999

Thanks for your article, its inspiring me. I am a PhD Student at the moment but also doing a parti time job and freelance webdesigner. So your tips is very useful and helping me.

http://www.gamezebo.com/ Carlos

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http://www.keyursavaliya.com Keyur savaliya

Denny Dover,
I am really enjoying your articles,read most of all.I am doing job with mfg. company in india and travelling across country since last 6 months,
After reading all your articles,i will also do the same what you do write now.I love trqavelling a lots.I am in search of establish business which i could run remotely.I am mechanical engineer and marketing enthusiast.

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